Triethylamine → Methyl 5-amino-6-methylnicotinate

HRID 541420Notes

Reaction equation

HRID 541420 reaction equation
Cl[C:2]1[N:11]=[C:10]([CH3:12])[C:9]([N+:13]([O-])=O)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C>CO.[Pd]>[NH2:13][C:9]1[C:10]([CH3:12])=[N:11][CH:2]=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86672545Methyl 2-chloro-6-methyl-5-nitronicotinate

Product 1

HCID 58662456Methyl 5-amino-6-methylnicotinateYield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A round-bottom flask, containing a solution of methyl 2-chloro-6-methyl-5-nitronicotinate (12.8 g, 55.5 mmol, 1.00 equiv) in methanol (120 mL) was purged with nitrogen. Triethylamine (15.0 g, 149 mmol, 2.68 equiv) and palladium on carbon (1.30 g) were added. After further purging the flask with nitrogen, the atmosphere was changed to hydrogen and the resulting solution was stirred for 2 days at room temperature under atmospheric pressure. After purging the system with nitrogen, the solids were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:50-1:5) as eluent to furnish 3.50 g (38%) of the title compound as a yellow solid.

Workup

  1. customwas purged with nitrogen
  2. customAfter further purging the flask with nitrogen
  3. customAfter purging the system with nitrogen
  4. customthe solids were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-a8e89d91545d49a08fe1597ddb02b6f6
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

Loading…